Aniline derivatives and fungicides containing them

ABSTRACT

Aniline derivatives of the formula ##STR1## where R is hydrogen, halogen, cyano, nitro, alkyl, cycloalkyl, alkenyl, alkoxy, haloalkyl, haloalkoxy, or substituted or unsubstituted phenyl, phenoxy, benzyl or benzyloxy, 
     m is an integer from 1 to 5 or the group ##STR2## α-naphthyl or β-naphthyl and X is hydrogen, alkyl or cycloalkyl, 
     their plant-tolerated acid addition salts and metal complexes, and their use for combating fungi.

The present invention relates to novel aniline derivatives of thegeneral formula I ##STR3## where R is hydrogen, halogen, cyano, nitro,C₁ -C₁₅ -alkyl, C₃ -C₆ -cycloalkyl, C₃ -C₆ -alkenyl, C₁ -C₄ -alkoxy,C₁ - or C₂ -haloalkyl, C₁ - or C₂ -haloalkoxy, unsubstituted orsubstituted phenyl, unsubstituted or substituted phenoxy, unsubstitutedor substituted benzyl or unsubstituted or substituted benzyloxy,

m is an integer of from 1 to 5 or the group ##STR4## α-naphthyl orβ-naphthyl and X is hydrogen, C₁ -C₆ -alkyl or C₃ -C₆ -cycloalkyl, andtheir plant-tolerated acid addition salts and metal complexes.

It is known that oxime ether derivatives, for example2-phenoxymethylphenylglyoxylic acid methyl ester O-methyl oxime, can beused as fungicides (EP-A-253213). However, their action is insufficientfor some indications.

It is an object of the present invention to provide novel fungicidalactive ingredients having an oxime ether structure.

We have found that this object is achieved by the aniline derivatives Idefined at the outset. The present invention furthermore relates to aprocess for the preparation of the aniline derivatives I and tofungicides which contain the aniline derivatives I as activeingredients.

The radicals stated in the general formula I may have, for example, thefollowing meanings: R may be identical or different and may be hydrogen,halogen, e.g. fluorine, chlorine, bromine or iodine, cyano, nitro, C₁-C₁₅ -alkyl, preferably C₁ -C₈ -alkyl, in particular C₁ -C₄ -alkyl, e.g.methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl,tert-butyl, pentyl, hexyl, n-heptyl, 1,1,3-trimethylbutyl, n-octyl,1,1,3,3-tetramethylbutyl, nonyl, decyl, dodecyl, tridecyl or tetradecyl,C₃ -C₆ -cycloalkyl, e.g. cyclopropyl, cyclopentyl or cyclohexyl, C₃ -C₆-alkenyl, e.g. 1-propenyl or 2-propenyl, C₁ -C₄ -alkoxy, e.g. methoxy,ethoxy, n-propoxy, isopropoxy, n-butoxy or tert-butoxy, C₁ - or C₂-haloalkyl, e.g. difluoromethyl, trifluoromethyl, trichloromethyl,dichloromethyl, trichloromethyl or pentafluoroethyl, C₁ - or C₂-haloalkoxy, e.g. trifluoromethoxy, difluoromethoxy, tetrafluoroethoxyor pentafluoroethoxy, unsubstituted or substituted phenyl, e.g. phenyl,C₁ -C₄ -alkylphenyl, such as 2-isopropylphenyl or 2-methylphenyl,halophenyl, such as 2-chlorophenyl, unsubstituted or substitutedphenoxy, e.g phenoxy, C₁ -C₄ -alkylphenoxy, such as 2-methylphenoxy,halophenoxy, such as 2-chlorophenoxy, unsubstituted or substitutedbenzyl, e.g. benzyl, halobenzyl, such as 2-chlorobenzyl, unsubstitutedor substituted benzyloxy, e.g. benzyloxy, halobenzyloxy or C₁ -C₄-alkylbenzyloxy, such as 2-chlorobenzyloxy, 2-methylbenzyloxy or4-tert-butylbenzyloxy. The alkyl, alkenyl, alkoxy and haloalkyl radicalsmay be straight-chain or branched. The same applies to the correspondingsubstituents of the phenyl, phenoxy, benzyl and benzyloxy radicals. Thenumber of substituents of the last-mentioned radicals may be from 1 to3.

Preferred radicals R are hydrogen, halogen, in particular fluorine, andC₁ -C₄ -alkyl, in particular methyl.

m is 1, 2, 3, 4 or 5, preferably 1, 2 or 3.

X is hydrogen, straight-chain or branched C₁ -C₆ -alkyl, preferably C₁-C₄ -alkyl, e.g. methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl,sec-butyl, tert-butyl, pentyl or hexyl, or C₃ -C₆ -cycloalkyl, e.g.cyclopropyl, cyclopentyl, cyclohexyl. X is in particular methyl.

The novel aniline derivatives I can also be converted by reaction withacids into plant-tolerated acid addition salts of the inorganic ororganic acids, for example into salts of hydrochloric acid, hydrobromicacid, nitric acid, oxalic acid, acetic acid, sulfuric acid, phosphoricacid or dodecylbenzenesulfonic acid. The activity of the salts is due tothe cation, so that the anion generally has no effect.

The compounds I may furthermore be converted into metal complexes byknown methods. This can be achieved by reacting these compounds withmetal salts, for example salts of the metals copper, zinc, iron,manganese or nickel, e.g. copper(II) chloride, zinc(II) chloride,iron(III) chloride, copper(II) nitrate, manganese(II) chloride ornickel(II) bromide.

Because of the C═N double bonds, the compounds I may occur both as Eisomers and as Z isomers. Both the individual isomeric compounds andmixtures thereof form subjects of the invention and can be used asfungicidal active ingredients.

The compounds I can be prepared, for example, by the following process:##STR5## A benzyl halide of the general formula II, where Hal ischlorine, bromine or iodine, is reacted with an aniline of the generalformula III, where R, m and X have the abovementioned meanings, in asuitable organic solvent, for example toluene or N,N-dimethylformamide,in the presence or absence of a suitable catalyst, such as potassiumiodide or sodium iodide, by a conventional method (J. March, AdvancedOrganic Chemistry, 3rd edition, 1985 pages 364-366, J. Wiley & Sons, NewYork) at from 20° to 120° C., preferably from 100° to 120° C.

The substituted benzyl halides of the general formula II where Hal ischloride or bromide are obtained by halogenating the2-methylphenylglyoxylic acid methyl ester O-methyl oxime IV by methodsknown from the literature. This is achieved, for example, using bromineor chlorine in an inert solvent (e.g. tetrachloromethane), with orwithout exposure to a light source (for example a 300 W Hg vapor lamp)or by reaction with N-chloro- or N-bromosuccinimide (Horner andWinkelmann, Angew. Chem. 71, (1959), 349). ##STR6##

Compound II in which Hal is iodide can be prepared by reaction withsodium iodide in acetone (Miller and Nunn, J. Chem. Soc., Perkin TransI, (1976), 416). 2-Methylphenylglyoxylic acid methyl ester O-methyloxime IV can be obtained by reacting methyl 2-methylphenylglyoxylate Vwith, for example, a) O-methylhydroxylamine hydrochloride or b)hydroxylamine hydrochloride to give the corresponding oxime andmethylating this oxime with a conventional methylating agent of theformula CH₃ --L in which L is a leaving group, e.g. chloride, bromide,iodide or methylsulfate (cf. DE-A-36 23 921). ##STR7##

Benzyl halides of the general formula II, where Hal is chloride, bromideor iodide, are furthermore obtained if a methyl2-halomethylphenyloxylate VI is a) reacted with O-methylhydroxylaminehydrochloride or b) reacted with hydroxylamine hydrochloride to give thecorresponding oxime and the latter is reacted with a methylating agentof the formula CH₃ --L, where L is a leaving group, e.g. chloride,bromide, iodide or methylsulfate (DE-A-36 23 921). ##STR8##

Methyl 2-halomethylphenylglyoxylates of the formula VI where Hal ischloride or bromide can be prepared by halogenating methyl2-methylphenylglyoxylate V by methods known from the literature. Thereaction is carried out, for example, using bromine or chlorine in aninert solvent (e.g. tetrachloromethane), with or without exposure to alight source (for example a 300 W Hg vapor lamp), or using N-chloro- orN-bromosuccinimide (Horner and Winkelmann, Angew. Chem. 71 (1959), 349).##STR9##

Compound VI in which Hal is iodide can be prepared from the chloride orbromide by reaction with sodium iodide in acetone by a method known fromthe literature (J. Chem. Soc., Perkin Trans. I, (1976), 416).

PREPARATION EXAMPLES EXAMPLE 1

a) 21.4 g (0.133 mol) of bromine are added, while stirring, to 27.6 g(0.133 mol) of 2-methylphenylglyoxylic acid methyl ester O-methyl oximedissolved in 400 ml of tetrachloromethane. Refluxing is then carried outfor four hours with exposure to a 300 W Hg vapor lamp. Thereafter, themixture is evaporated down, the residue is taken up in ethylacetate/water and the solution is washed with water, dried with sodiumsulfate and evaporated down. The crude product is purified bychromatography over silica gel using 9:1 cyclohexane/ethyl acetate. 17.4g (46% of theory) of 2-bromomethylphenylglyoxylic acid methyl esterO-methyl oxime are obtained as an oil.

b) 6.4 g (60 mmol) of N-methylaniline, 8.6 g (30 mmol) of2-bromomethylphenylglyoxylic acid methyl ester O-methyl oxime and about100 mg of potassium iodide in 100 ml of toluene are refluxed for 7 hourswhile stirring. The mixture is cooled, washed several times with water,dried over sodium sulfate and then evaporated down. 9 g (96% of theory)of 2-[(N-methyl-N-phenyl)aminomethyl]-phenylglyoxylic acid methyl esterO-methyl oxime (Table 1, No. 1) are obtained (mp.=90°-92° C.). ¹ H-NMR:δ=2.95 (s, 3H); 3.75 (s, 3H); 4.05 (s, 3H); 4.35 (s, 2H); 6.65-7.35 (m,9H).

The active ingredients shown in Table 1 can be prepared similarly toprocesses described by J. March, Advanced Organic Chemistry, 3rdedition, 1985, pages 364-366 and in Example 1.

                  TABLE 1                                                         ______________________________________                                         ##STR10##                     (I)                                                                               mp (°C.)/                           No.   R.sub.m           X          IR (cm.sup.-1)                             ______________________________________                                        1     H                 CH.sub.3   90-92/                                                                        2935,1725,                                                                    1600,1507,                                                                    1215,1069,                                                                    1017,751                                   2     2-F               CH.sub.3                                              3     3-F               CH.sub.3   101-102/                                                                      2935,1723,                                                                    1620,1502,                                                                    1214,1066,                                                                    1014,761                                   4     4-F               CH.sub.3   73-75/                                                                        2940,1725,                                                                    1512,1227,                                                                    1069,1017,                                                                    819                                        5     2,3-F.sub.2       CH.sub.3                                              6     2,4-F.sub.2       CH.sub.3                                              7     2,4,6-F.sub.3     CH.sub.3                                              8     2,3,4,5,6-F.sub.5 CH.sub.3                                              9     2-Cl              CH.sub.3                                              10    3-Cl              CH.sub.3                                              11    4-Cl              CH.sub.3                                              12    2,3-Cl.sub.2      CH.sub.3                                              13    2,4-Cl.sub.2      CH.sub.3                                              14    2,5-Cl.sub.2      CH.sub.3                                              15    2,6-Cl.sub.2      CH.sub.3                                              16    3,4-Cl.sub.2      CH.sub.3                                              17    3,5-Cl.sub.2      CH.sub.3                                              18    2,3,4-Cl.sub.3    CH.sub.3                                              19    2,3,5-Cl.sub.3    CH.sub.3                                              20    2,3,6-Cl.sub.3    CH.sub.3                                              21    2,4,5-Cl.sub.3    CH.sub.3                                              22    2,4,6-Cl.sub.3    CH.sub.3                                              23    3,4,5-Cl.sub.3    CH.sub.3                                              24    2,3,4,6-Cl.sub.4  CH.sub.3                                              25    2,3,5,6-Cl.sub.4  CH.sub.3                                              26    2,3,4,5,6-Cl.sub.5                                                                              CH.sub.3                                              27    2-Br              CH.sub.3                                              28    3-Br              CH.sub.3                                              29    4-Br              CH.sub.3                                              30    2,4-Br.sub.2      CH.sub.3                                              31    2,5-Br.sub.2      CH.sub.3                                              32    2,6-Br.sub.2      CH.sub.3                                              33    2,4,6-Br.sub.3    CH.sub.3                                              34    2,3,4,5,6-Br.sub.5                                                                              CH.sub.3                                              35    2-I               CH.sub.3                                              36    3-I               CH.sub.3                                              37    4-I               CH.sub.3                                              38    2,4-I.sub.2       CH.sub.3                                              39    2-Cl, 3-F         CH.sub.3                                              40    2-Cl, 4-F         CH.sub.3                                              41    2-Cl, 5-F         CH.sub.3                                              42    2-Cl, 6-F         CH.sub.3                                              43    2-Cl, 3-Br        CH.sub.3                                              44    2-Cl, 4-Br        CH.sub.3                                              45    2-Cl, 5-Br        CH.sub.3                                              46    2-Cl, 6-Br        CH.sub.3                                              47    2-Br, 3-Cl        CH.sub.3                                              48    2-Br, 4-Cl        CH.sub.3                                              49    2-Br, 5-Cl        CH.sub.3                                              50    2-Br, 3-F         CH.sub.3                                              51    2-Br, 4-F         CH.sub.3                                              52    2-Br, 5-F         CH.sub.3                                              53    2-Br, 6-F         CH.sub.3                                              54    2-F, 3-Cl         CH.sub.3                                              55    2-F, 4-Cl         CH.sub.3                                              56    2-F, 5-Cl         CH.sub.3                                              57    3-Cl, 4-F         CH.sub.3                                              58    3-Cl, 5-F         CH.sub.3                                              59    3-Cl, 4-Br        CH.sub.3                                              60    3-Cl, 5-Br        CH.sub.3                                              61    3-F, 4-Cl         CH.sub.3                                              62    3-F, 4-Br         CH.sub.3                                              63    3-Br, 4-Cl        CH.sub.3                                              64    3-Br, 4-F         CH.sub.3                                              65    2,6-Cl.sub.2, 4-Br                                                                              CH.sub.3                                              66    2-CH.sub.3        CH.sub.3                                              67    3-CH.sub.3        CH.sub.3   68-72/                                                                        2935,1755,                                                                    1603,1213,                                                                    1068,1017,                                                                    767                                        68    4-CH.sub.3        CH.sub.3   80-82/                                                                        2940,1726,                                                                    1522,1321,                                                                    1215,1068,                                                                    1018,805                                   69    2,3-(CH.sub.3).sub.2                                                                            CH.sub.3                                              70    2,4-(CH.sub.3).sub.2                                                                            CH.sub.3                                              71    2,5-(CH.sub.3).sub.2                                                                            CH.sub.3                                              72    2,6-(CH.sub.3).sub.2                                                                            CH.sub.3                                              73    3,4-(CH.sub.3).sub.2                                                                            CH.sub.3                                              74    3,5-(CH.sub.3).sub.2                                                                            CH.sub.3                                              75    2,3,4-(CH.sub.3).sub.3                                                                          CH.sub.3                                              76    2,3,5-(CH.sub.3).sub.3                                                                          CH.sub.3                                              77    2,3,6-(CH.sub.3).sub.3                                                                          CH.sub.3                                              78    2,4,5-(CH.sub.3).sub.3                                                                          CH.sub.3                                              79    2,4,6-(CH.sub.3).sub.3                                                                          CH.sub.3                                              80    3,4,5-(CH.sub.3).sub.3                                                                          CH.sub.3                                              81    2,3,4,6-(CH.sub.3).sub.4                                                                        CH.sub.3                                              82    2,3,5,6-(CH.sub.3).sub.4                                                                        CH.sub.3                                              83    2,3,4,5,6-(CH.sub.3).sub.5                                                                      CH.sub.3                                              84    2-C.sub.2 H.sub.5 CH.sub.3                                              85    3-C.sub.2 H.sub.5 CH.sub. 3                                             86    4-C.sub.2 H.sub.5 CH.sub.3                                              87    2,4-(C.sub.2 H.sub.5).sub.2                                                                     CH.sub.3                                              88    2,6-(C.sub.2 H.sub.5).sub.2                                                                     CH.sub.3                                              89    3,5-(C.sub.2 H.sub.5).sub.2                                                                     CH.sub.3                                              90    2,4,6-(C.sub.2 H.sub.5).sub.3                                                                   CH.sub.3                                              91    2-n-C.sub.3 H.sub.7                                                                             CH.sub.3                                              92    3-n-C.sub.3 H.sub.7                                                                             CH.sub.3                                              93    4-n-C.sub.3 H.sub.7                                                                             CH.sub.3                                              94    2-i-C.sub.3 H.sub.7                                                                             CH.sub.3                                              95    3-i-C.sub.3 H.sub.7                                                                             CH.sub.3                                              96    4-i-C.sub.3 H.sub.7                                                                             CH.sub.3                                              97    2,4-(i-C.sub.3 H.sub.7).sub.2                                                                   CH.sub.3                                              98    2,6-(i-C.sub.3 H.sub.7).sub.2                                                                   CH.sub.3                                              99    3,5-(i-C.sub.3 H.sub.7).sub.2                                                                   CH.sub.3                                              100   2,4,6-(i-C.sub.3 H.sub.7).sub.3                                                                 CH.sub.3                                              101   2-s-C.sub.4 H.sub.9                                                                             CH.sub.3                                              102   3-s-C.sub.4 H.sub.9                                                                             CH.sub.3                                              103   4-s-C.sub.4 H.sub.9                                                                             CH.sub.3                                              104   2-t-C.sub.4 H.sub.9                                                                             CH.sub.3                                              105   3-t-C.sub.4 H.sub.9                                                                             CH.sub.3                                              106   4-t-C.sub.4 H.sub.9                                                                             CH.sub.3                                              107   2,3-(t-C.sub.4 H.sub.9).sub.2                                                                   CH.sub.3                                              108   2,4-(t-C.sub.4 H.sub.9).sub.2                                                                   CH.sub.3                                              109   2,5-(t-C.sub.4 H.sub.9).sub.2                                                                   CH.sub.3                                              110   2,6-(t-C.sub.4 H.sub.9).sub.2                                                                   CH.sub.3                                              111   3,5-(t-C.sub.4 H.sub.9).sub.2                                                                   CH.sub.3                                              112   2,4,6-(t-C.sub.4 H.sub.9).sub.3                                                                 CH.sub.3                                              113   4-n-C.sub.9 H.sub.19                                                                            CH.sub.3                                              114   4-n-C.sub.12 H.sub.25                                                                           CH.sub.3                                              115   3-n-C.sub.15 H.sub.31                                                                           CH.sub.3                                              116   4-(1,1,3,3,-tetramethylbutyl)                                                                   CH.sub.3                                              117   4-(1,1,3,-trimethylbutyl)                                                                       CH.sub.3                                              118   2-t-C.sub.4 H.sub.9, 4-CH.sub.3                                                                 CH.sub.3                                              119   2-t-C.sub.4 H.sub.9, 5-CH.sub.3                                                                 CH.sub.3                                              120   2,6-(t-C.sub.4 H.sub.9).sub.2, 4-CH.sub.3                                                       CH.sub.3                                              121   2-CH.sub.3, 4-t-C.sub.4 H.sub.9                                                                 CH.sub.3                                              122   2-CH.sub.3, 6-t-C.sub.4 H.sub.9                                                                 CH.sub.3                                              123   2-CH.sub.3, 4-i-C.sub.3 H.sub.7                                                                 CH.sub.3                                              124   2-CH.sub.3, 5-i-C.sub.3 H.sub.7                                                                 CH.sub.3                                              125   3-CH.sub.3, 4-i-C.sub.3 H.sub.7                                                                 CH.sub.3                                              126   2-i-C.sub.3 H.sub.7, 5-CH.sub.3                                                                 CH.sub.3                                              127   2,4-(t-C.sub.4 H.sub.9).sub.2, 6-i-C.sub.3 H.sub.7                                              CH.sub.3                                              128   2-allyl (C.sub.3 H.sub.5)                                                                       CH.sub.3                                              129   3-allyl           CH.sub.3                                              130   4-allyl           CH.sub.3                                              131   2-C.sub.3 H.sub.5, 6-CH.sub.3                                                                   CH.sub.3                                              132   2-cyclo-C.sub.6 H.sub.11                                                                        CH.sub.3                                              133   3-cyclo-C.sub.6 H.sub.11                                                                        CH.sub.3                                              134   4-cyclo-C.sub.6 H.sub.11                                                                        CH.sub. 3                                             135   2,4-(cyclo-C.sub.6 H.sub.11).sub.2, 6-CH.sub.3                                                  CH.sub.3                                              136   2-CH.sub.3, 4-cyclo-C.sub.6 H.sub.11                                                            CH.sub.3                                              137   2-CH.sub.3,       CH.sub.3                                                    4-(1,1,3,3-tetramethylbutyl)                                            138   2-CH.sub.2 C.sub.6 H.sub.5                                                                      CH.sub.3                                              139   3-CH.sub.2 C.sub.6 H.sub.5                                                                      CH.sub.3                                              140   4-CH.sub.2 C.sub.6 H.sub.5                                                                      CH.sub.3                                              141   2-CH.sub.2 C.sub.6 H.sub.5, 4-CH.sub.3                                                          CH.sub.3                                              142   2-CH.sub.3, 4-CH.sub.2 C.sub.6 H.sub.5                                                          CH.sub.3                                              143   2-C.sub.6 H.sub.5 CH.sub.3                                              144   3-C.sub.6 H.sub.5 CH.sub.3                                              145   4-C.sub.6 H.sub.5 CH.sub.3                                              146   4-(2-i-C.sub.3 H.sub.7C.sub.6 H.sub.4)                                                          CH.sub.3                                              147   4-C.sub.6 H.sub.5, 2,6-(CH.sub.3).sub.2                                                         CH.sub.3                                              148   2-Cl, 4-C.sub.6 H.sub.5                                                                         CH.sub.3                                              149   2-Br, 4-C.sub.6 H.sub.5                                                                         CH.sub.3                                              150   2-C.sub.6 H.sub.5, 4-Cl                                                                         CH.sub.3                                              151   2-C.sub.6 H.sub.5, 4-Br                                                                         CH.sub.3                                              152   2-CH.sub.2 C.sub.6 H.sub.5, 4-Cl                                                                CH.sub.3                                              153   2-CH.sub.2 C.sub.6 H.sub.5, 4-Br                                                                CH.sub.3                                              154   2-Cl, 4-CH.sub.2 C.sub.6 H.sub.5                                                                CH.sub.3                                              155   2-Br, 4-CH.sub.2 C.sub.6 H.sub. 5                                                               CH.sub.3                                              156   2-cyclo-C.sub.6 H.sub.11, 4-Cl                                                                  CH.sub.3                                              157   2-cyclo-C.sub.6 H.sub.11, 4-Br                                                                  CH.sub.3                                              158   2-Cl, 4-cyclo-C.sub.6 H.sub.11                                                                  CH.sub.3                                              159   2-Br, 4-cyclo-C.sub.6 H.sub.11                                                                  CH.sub.3                                              160   2-OCH.sub.3       CH.sub.3                                              161   3-OCH.sub.3       CH.sub.3                                              162   4-OCH.sub.3       CH.sub.3                                              163   2,4-(OCH.sub.3).sub.2                                                                           CH.sub.3                                              164   2-OC.sub.2 H.sub.5                                                                              CH.sub.3                                              165   3-OC.sub.2 H.sub.5                                                                              CH.sub.3                                              166   4-OC.sub.2 H.sub.5                                                                              CH.sub.3                                              167   2-OCH.sub.2 C.sub.6 H.sub.5                                                                     CH.sub.3                                              168   3-OCH.sub.2 C.sub.6 H.sub.5                                                                     CH.sub.3                                              169   4-OCH.sub.2 C.sub.6 H.sub.5                                                                     CH.sub.3                                              170   2-O-t-C.sub.4 H.sub.9                                                                           CH.sub.3                                              171   3-O-t-C.sub.4 H.sub.9                                                                           CH.sub.3                                              172   4-O-t-C.sub.4 H.sub.9                                                                           CH.sub.3                                              173   2-OC.sub.6 H.sub.5                                                                              CH.sub.3                                              174   3-OC.sub.6 H.sub.5                                                                              CH.sub.3                                              175   4-OC.sub.6 H.sub.5                                                                              CH.sub.3                                              176   2-CF.sub.3        CH.sub.3                                              177   3-CF.sub.3        CH.sub.3                                              178   4-CF.sub.3        CH.sub.3                                              179   2-OCF.sub.3       CH.sub.3                                              180   3-OCF.sub.3       CH.sub.3                                              181   4-OCF.sub.3       CH.sub.3                                              182   3-OCH.sub.2 CHF.sub.2                                                                           CH.sub.3                                              183   3-OCF.sub.2 CHF.sub.2                                                                           CH.sub.3                                              184   3-OC.sub.2 F.sub.5                                                                              CH.sub.3                                              185   2-NO.sub.2        CH.sub.3                                              186   3-NO.sub.2        CH.sub.3                                              187   4-NO.sub.2        CH.sub.3                                              188   2-CN              CH.sub.3                                              189   3-CN              CH.sub.3                                              190   4-CN              CH.sub.3                                              191   2-CH.sub.3, 3-Cl  CH.sub.3                                              192   2-CH.sub.3, 4-Cl  CH.sub.3                                              193   2-CH.sub.3, 5-Cl  CH.sub.3                                              194   2-CH.sub.3, 6-Cl  CH.sub.3                                              195   2-CH.sub.3, 3-F   CH.sub.3                                              196   2-CH.sub.3, 4-F   CH.sub.3                                              197   2-CH.sub.3, 5-F   CH.sub.3                                              198   2-CH.sub.3, 6-F   CH.sub.3                                              199   2-CH.sub.3, 3-Br  CH.sub.3                                              200   2-CH.sub.3, 4-Br  CH.sub.3                                              201   2-CH.sub.3, 5-Br  CH.sub.3                                              202   2-CH.sub.3, 6-Br  CH.sub.3                                              203   2-Cl, 3-CH.sub.3  CH.sub.3                                              204   2-Cl, 4-CH.sub.3  CH.sub.3                                              205   2-Cl, 5-CH.sub.3  CH.sub.3                                              206   2-F, 3-CH.sub.3   CH.sub.3                                              207   2-F, 4-CH.sub.3   CH.sub.3                                              208   2-F, 5-CH.sub.3   CH.sub.3                                              209   2-Br, 3-CH.sub.3  CH.sub.3                                              210   2-Br, 4-CH.sub.3  CH.sub.3                                              211   2-Br, 5-CH.sub.3  CH.sub.3                                              212   3-CH.sub.3, 4-Cl  CH.sub.3                                              213   3-CH.sub.3, 5-Cl  CH.sub.3                                              214   3-CH.sub.3, 4-F   CH.sub.3                                              215   3-CH.sub.3, 5-F   CH.sub.3                                              216   3-CH.sub.3, 4-Br  CH.sub.3                                              217   3-CH.sub.3, 5-Br  CH.sub.3                                              218   3-F, 4-CH.sub.3   CH.sub.3                                              219   3-Cl, 4-CH.sub.3  CH.sub.3                                              220   3-Br, 4-CH.sub.3  CH.sub.3                                              221   2-Cl, 4,5-(CH.sub.3).sub.2                                                                      CH.sub.3                                              222   2-Br, 4,5-(CH.sub.3).sub.2                                                                      CH.sub.3                                              223   2-Cl, 3,5-(CH.sub.3).sub.2                                                                      CH.sub.3                                              224   2-Br, 3,5-(CH.sub.3).sub.2                                                                      CH.sub.3                                              225   2,6-Cl.sub.2, 4-CH.sub.3                                                                        CH.sub.3                                              226   2,6-F.sub.2, 4-CH.sub.3                                                                         CH.sub.3                                              227   2,6-Br.sub.2, 4-CH.sub.3                                                                        CH.sub.3                                              228   2,4-Cl.sub.2, 6-CH.sub.3                                                                        CH.sub.3                                              229   2,4-F.sub.2, 6-CH.sub.3                                                                         CH.sub.3                                              230   2,4-Br.sub.2, 6-CH.sub.3                                                                        CH.sub.3                                              231   2,6-(CH.sub.3).sub.2, 4-F                                                                       CH.sub.3                                              232   2,6-(CH.sub.3).sub.2, 4-Cl                                                                      CH.sub.3                                              233   2,6-(CH.sub.3).sub.2, 4-Br                                                                      CH.sub.3                                              234   3,5-(CH.sub.3).sub.2, 4-F                                                                       CH.sub.3                                              235   3,5-(CH.sub.3).sub.2, 4-Cl                                                                      CH.sub.3                                              236   3,5-(CH.sub.3).sub.2, 4-Br                                                                      CH.sub.3                                              237   2,3,6-(CH.sub.3).sub.3, 4-F                                                                     CH.sub.3                                              238   2,3,6-(CH.sub.3).sub.3, 4-Cl                                                                    CH.sub.3                                              239   2,3,6-(CH.sub.3).sub.3, 4-Br                                                                    CH.sub.3                                              240   2,4-(CH.sub.3).sub.2, 6-F                                                                       CH.sub.3                                              241   2,4-(CH.sub.3).sub.2 , 6-Cl                                                                     CH.sub.3                                              242   2,4-(CH.sub.3).sub.2, 6-Br                                                                      CH.sub.3                                              243   2-i-C.sub.3 H.sub.7, 4-Cl, 5-CH.sub.3                                                           CH.sub.3                                              244   2-CH.sub.3, 4-Cl, 5-i-C.sub.3 H.sub.7                                                           CH.sub.3                                              245   2-Cl, 3-i-C.sub.3 H.sub.7                                                                       CH.sub.3                                              246   2-Cl, 4-i-C.sub.3 H.sub.7                                                                       CH.sub.3                                              247   2-Cl, 4-NO.sub.2  CH.sub.3                                              248   2-NO.sub.2, 4-Cl  CH.sub.3                                              249   2-OCH.sub.3, 5-NO.sub.2                                                                         CH.sub.3                                              250   2,4-Cl.sub.2, 5-NO.sub.2                                                                        CH.sub.3                                              251   2,4-Cl.sub.2, 6-NO.sub.2                                                                        CH.sub.3                                              252   2,6-Cl.sub.2, 4-NO.sub.2                                                                        CH.sub.3                                              253   2,6-Br.sub.2, 4-NO.sub.2                                                                        CH.sub.3                                              254   2,6-I.sub.2, 4-NO.sub.2                                                                         CH.sub.3                                              255   H                 C.sub.2 H.sub.5                                       256   2-F               C.sub.2 H.sub.5                                       257   3-F               C.sub.2 H.sub.5                                       258   4-F               C.sub.2 H.sub.5                                       259   2,3-F.sub.2       C.sub.2 H.sub.5                                       260   2,4-F.sub.2       C.sub.2 H.sub.5                                       261   2,4,6-F.sub.3     C.sub.2 H.sub.5                                       262   2,3,4,5,6-F.sub.5 C.sub.2 H.sub.5                                       263   2-Cl              C.sub.2 H.sub.5                                       264   3-Cl              C.sub.2 H.sub.5                                       265   4-Cl              C.sub.2 H.sub.5                                       266   2,3-Cl.sub.2      C.sub.2 H.sub.5                                       267   2,4-Cl.sub.2      C.sub.2 H.sub.5                                       268   2,5-Cl.sub.2      C.sub. 2 H.sub.5                                      269   2,6-Cl.sub.2      C.sub.2 H.sub.5                                       270   3,4-Cl.sub.2      C.sub.2 H.sub.5                                       271   3,5-Cl.sub.2      C.sub.2 H.sub.5                                       272   2,3,4-Cl.sub.3    C.sub.2 H.sub.5                                       273   2,3,5-Cl.sub.3    C.sub.2 H.sub.5                                       274   2,3,6-Cl.sub.3    C.sub.2 H.sub.5                                       275   2,4,5-Cl.sub.3    C.sub.2 H.sub.5                                       276   2,4,6-Cl.sub.3    C.sub.2 H.sub.5                                       277   3,4,5-Cl.sub.3    C.sub.2 H.sub.5                                       278   2,3,4,6-Cl.sub.4  C.sub.2 H.sub.5                                       279   2,3,5,6-Cl.sub.4  C.sub.2 H.sub.5                                       280   2,3,4,5,6-Cl.sub.5                                                                              C.sub.2 H.sub.5                                       281   2-Br              C.sub.2 H.sub.5                                       282   3-Br              C.sub.2 H.sub.5                                       283   4-Br              C.sub.2 H.sub.5                                       284   2,4-Br.sub.2      C.sub.2 H.sub.5                                       285   2,5-Br.sub.2      C.sub.2 H.sub.5                                       286   2,6-Br.sub.2      C.sub.2 H.sub.5                                       287   2,4,6-Br.sub.3    C.sub.2 H.sub.5                                       288   2,3,4,5,6-Br.sub.5                                                                              C.sub.2 H.sub.5                                       289   2-I               C.sub.2 H.sub.5                                       290   3-I               C.sub.2 H.sub.5                                       291   4-I               C.sub.2 H.sub.5                                       292   2,4-I.sub.2       C.sub.2 H.sub.5                                       293   2-Cl, 3-F         C.sub.2 H.sub.5                                       294   2-Cl, 4-F         C.sub.2 H.sub.5                                       295   2-Cl, 5-F         C.sub.2 H.sub.5                                       296   2-Cl, 3-F         C.sub.2 H.sub.5                                       297   2-Cl, 3-Br        C.sub.2 H.sub.5                                       298   2-Cl, 4-Br        C.sub.2 H.sub.5                                       299   2-Cl, 5-Br        C.sub.2 H.sub.5                                       300   2-Cl, 6-Br        C.sub.2 H.sub.5                                       301   2-Br, 3-Cl        C.sub.2 H.sub.5                                       302   2-Br, 4-Cl        C.sub.2 H.sub.5                                       303   2-Br, 5-Cl        C.sub.2 H.sub.5                                       304   2-Br, 3-F         C.sub.2 H.sub.5                                       305   2-Br, 4-F         C.sub.2 H.sub.5                                       306   2-Br, 5-F         C.sub.2 H.sub.5                                       307   2-Br, 6-F         C.sub.2 H.sub.5                                       308   2-F, 3-Cl         C.sub.2 H.sub.5                                       309   2-F, 4-Cl         C.sub.2 H.sub.5                                       310   2-F, 5-Cl         C.sub.2 H.sub.5                                       311   3-Cl, 4-F         C.sub.2 H.sub.5                                       312   3-Cl, 5-F         C.sub.2 H.sub.5                                       313   3-Cl, 4-Br        C.sub.2 H.sub.5                                       314   3-Cl, 5-Br        C.sub.2 H.sub.5                                       315   3-F, 4-Cl         C.sub.2 H.sub.5                                       316   3-F, 4-Br         C.sub.2 H.sub.5                                       317   3-Br, 4-Cl        C.sub.2 H.sub.5                                       318   3-Br, 4-F         C.sub.2 H.sub.5                                       319   2,6-Cl.sub.2, 4-Br                                                                              C.sub.2 H.sub.5                                       320   2-CH.sub.3        C.sub.2 H.sub.5                                       321   3-CH.sub.3        C.sub.2 H.sub.5                                       322   4-CH.sub.3        C.sub.2 H.sub.5                                       323   2,3-(CH.sub.3).sub.2                                                                            C.sub.2 H.sub.5                                       324   2,4-(CH.sub.3).sub.2                                                                            C.sub.2 H.sub.5                                       325   2,5-(CH.sub.3).sub.2                                                                            C.sub.2 H.sub.5                                       326   2,6-(CH.sub.3).sub.2                                                                            C.sub.2 H.sub.5                                       327   3,4-(CH.sub.3).sub.2                                                                            C.sub.2 H.sub.5                                       328   3,5-(CH.sub.3).sub.2                                                                            C.sub.2 H.sub.5                                       329   2,3,4-(CH.sub.3).sub.3                                                                          C.sub.2 H.sub.5                                       330   2,3,5-(CH.sub.3).sub.3                                                                          C.sub.2 H.sub.5                                       331   2,3,6-(CH.sub.3).sub.3                                                                          C.sub.2 H.sub.5                                       332   2,4,5-(CH.sub.3).sub.3                                                                          C.sub.2 H.sub.5                                       333   2,4,6-(CH.sub.3).sub.3                                                                          C.sub.2 H.sub.5                                       334   3,4,5-(CH.sub.3).sub.3                                                                          C.sub.2 H.sub.5                                       335   2,3,4,6-(CH.sub.3).sub.4                                                                        C.sub.2 H.sub.5                                       336   2,3,4,6-(CH.sub.3).sub.4                                                                        C.sub.2 H.sub.5                                       337   2,3,4,5,6-(CH.sub.3).sub.5                                                                      C.sub.2 H.sub.5                                       338   2-C.sub.2 H.sub.5 C.sub.2 H.sub.5                                       339   3-C.sub.2 H.sub.5 C.sub.2 H.sub.5                                       340   4-C.sub.2 H.sub.5 C.sub.2 H.sub.5                                       341   2,4-(C.sub.2 H.sub.5).sub.2                                                                     C.sub.2 H.sub.5                                       342   2,6-(C.sub.2 H.sub.5).sub.2                                                                     C.sub.2 H.sub.5                                       343   3,5-(C.sub.2 H.sub.5).sub.2                                                                     C.sub.2 H.sub.5                                       344   2,4,6-(C.sub.2 H.sub.5).sub.3                                                                   C.sub.2 H.sub.5                                       345   2-n-C.sub.3 H.sub.7                                                                             C.sub.2 H.sub.5                                       346   3-n-C.sub.3 H.sub.7                                                                             C.sub.2 H.sub. 5                                      347   4-n-C.sub.3 H.sub.7                                                                             C.sub.2 H.sub.5                                       348   2-i-C.sub.3 H.sub.7                                                                             C.sub.2 H.sub.5                                       349   3-i-C.sub.3 H.sub.7                                                                             C.sub.2 H.sub.5                                       350   4-i-C.sub.3 H.sub.7                                                                             C.sub.2 H.sub.5                                       351   2,4-(i-C.sub.3 H.sub.7).sub.2                                                                   C.sub.2 H.sub.5                                       352   2,6-(i-C.sub.3 H.sub.7).sub.2                                                                   C.sub.2 H.sub.5                                       353   2,4,6-(i-C.sub.3 H.sub.7).sub.3                                                                 C.sub.2 H.sub.5                                       354   2,4,6-(i-C.sub.3 H.sub.7).sub.3                                                                 C.sub.2 H.sub.5                                       355   2-s-C.sub.4 H.sub.9                                                                             C.sub.2 H.sub.5                                       356   3-s-C.sub.4 H.sub.9                                                                             C.sub.2 H.sub.5                                       357   4-s-C.sub.4 H.sub.9                                                                             C.sub.2 H.sub.5                                       358   2-t-C.sub.4 H.sub.9                                                                             C.sub.2 H.sub.5                                       359   3-t-C.sub.4 H.sub.9                                                                             C.sub.2 H.sub.5                                       360   4-t-C.sub.4 H.sub.9                                                                             C.sub.2 H.sub.5                                       361   2,3-(t-C.sub.4 H.sub.9).sub.2                                                                   C.sub.2 H.sub.5                                       362   2,4-(t-C.sub.4 H.sub.9).sub.2                                                                   C.sub.2 H.sub.5                                       363   2,5-(t-C.sub.4 H.sub.9).sub.2                                                                   C.sub.2 H.sub.5                                       364   2,6-(t-C.sub.4 H.sub.9).sub.2                                                                   C.sub.2 H.sub.5                                       365   3,5-(t-C.sub.4 H.sub.9).sub.2                                                                   C.sub.2 H.sub.5                                       366   2,4,6-(t-C.sub.4 H.sub.9).sub.3                                                                 C.sub.2 H.sub. 5                                      367   4-n-C.sub.9 H.sub.19                                                                            C.sub.2 H.sub.5                                       368   4-n-C.sub.12 H.sub.25                                                                           C.sub.2 H.sub.5                                       369   3-n-C.sub.15 H.sub.31                                                                           C.sub.2 H.sub.5                                       370   4-(1,1,3,3,-tetramethylbutyl)                                                                   C.sub.2 H.sub.5                                       371   4-(1,1,3,-trimethylbutyl)                                                                       C.sub.2 H.sub.5                                       372   2-t-C.sub.4 H.sub.9, 4-CH.sub.3                                                                 C.sub.2 H.sub.5                                       373   2-t-C.sub.4 H.sub.9, 5-CH.sub.3                                                                 C.sub.2 H.sub.5                                       374   2,6-(t-C.sub.4 H.sub.9).sub.2, 4-CH.sub.3                                                       C.sub.2 H.sub.5                                       375   2-CH.sub.3, 4-t-C.sub.4 H.sub.9                                                                 C.sub.2 H.sub.5                                       376   2-CH.sub.3, 6-t-C.sub.4 H.sub.9                                                                 C.sub.2 H.sub.5                                       377   2-CH.sub.3, 4-i-C.sub.3 H.sub.7                                                                 C.sub.2 H.sub.5                                       378   2-CH.sub.3, 5-i-C.sub.3 H.sub.7                                                                 C.sub.2 H.sub.5                                       379   3-CH.sub.3, 4-i-C.sub.3 H.sub.7                                                                 C.sub.2 H.sub.5                                       380   2-i-C.sub.3 H.sub.7, 5-CH.sub.3                                                                 C.sub.2 H.sub.5                                       381   2,4-(t-C.sub.4 H.sub.9).sub.2, 6-i-C.sub.3 H.sub.7                                              C.sub.2 H.sub.5                                       382   2-allyl (C.sub.3 H.sub.5)                                                                       C.sub.2 H.sub.5                                       383   3-allyl           C.sub.2 H.sub.5                                       384   4-allyl           C.sub.2 H.sub.5                                       385   2-C.sub.3 H.sub.5, 6-CH.sub.3                                                                   C.sub.2 H.sub. 5                                      386   2-cyclo-C.sub.6 H.sub.11                                                                        C.sub.2 H.sub.5                                       387   3-cyclo-C.sub.6 H.sub.11                                                                        C.sub.2 H.sub.5                                       388   4-cyclo-C.sub.6 H.sub.11                                                                        C.sub.2 H.sub.5                                       389   2,4-(cyclo-C.sub.6 H.sub.11).sub.2, 6-CH.sub.3                                                  C.sub.2 H.sub.5                                       390   2-CH.sub.3, 4-cyclo-C.sub.6 H.sub.11                                                            C.sub.2 H.sub.5                                       391   2-CH.sub.3,       C.sub.2 H.sub.5                                             4-(1,1,3,3-tetramethylbutyl)                                            392   2-CH.sub.2 C.sub.6 H.sub.5                                                                      C.sub.2 H.sub.5                                       393   3-CH.sub.2 C.sub.6 H.sub.5                                                                      C.sub.2 H.sub.5                                       394   4-CH.sub.2 C.sub.6 H.sub.5                                                                      C.sub.2 H.sub.5                                       395   2-CH.sub.2 C.sub.6 H.sub.5, 4-CH.sub.3                                                          C.sub.2 H.sub.5                                       396   2-CH.sub.3, 4-CH.sub.2 C.sub.6 H.sub.5                                                          C.sub.2 H.sub.5                                       397   2-C.sub.6 H.sub.5 C.sub.2 H.sub.5                                       398   3-C.sub.6 H.sub.5 C.sub.2 H.sub.5                                       399   4-C.sub.6 H.sub.5 C.sub.2 H.sub.5                                       400   4-(2-i-C.sub.3 H.sub.7C.sub.6 H.sub.4)                                                          C.sub.2 H.sub.5                                       401   4-C.sub.6 H.sub.5, 2,6-(CH.sub.3).sub.2                                                         C.sub.2 H.sub.5                                       402   2-Cl, 4-C.sub.6 H.sub.5                                                                         C.sub.2 H.sub.5                                       403   2-Br, 4-C.sub.6 H.sub.5                                                                         C.sub.2 H.sub.5                                       404   2-C.sub.6 H.sub.5, 4-Cl                                                                         C.sub.2 H.sub.5                                       405   2-C.sub.6 H.sub.5, 4-Br                                                                         C.sub.2 H.sub.5                                       406   2-CH.sub.2 C.sub.6 H.sub.5, 4-Cl                                                                C.sub.2 H.sub.5                                       407   2-CH.sub.2 C.sub.6 H.sub.5, 4-Br                                                                C.sub.2 H.sub.5                                       408   2-Cl, 4-CH.sub.2 C.sub.6 H.sub.5                                                                C.sub.2 H.sub.5                                       409   2-Br, 4-CH.sub.2 C.sub.6 H.sub.5                                                                C.sub.2 H.sub.5                                       410   2-cyclo-C.sub.6 H.sub.11, 4-Cl                                                                  C.sub.2 H.sub.5                                       411   2-cyclo-C.sub.6 H.sub.11, 4-Br                                                                  C.sub.2 H.sub.5                                       412   2-Cl, 4-cyclo-C.sub.6 H.sub.11                                                                  C.sub.2 H.sub.5                                       413   2-Br, 4-cyclo-C.sub.6 H.sub.11                                                                  C.sub.2 H.sub.5                                       414   2-OCH.sub.3       C.sub.2 H.sub.5                                       415   3-OCH.sub.3       C.sub.2 H.sub.5                                       416   4-OCH.sub.3       C.sub.2 H.sub.5                                       417   2,4-(OCH.sub.3).sub.2                                                                           C.sub.2 H.sub.5                                       418   2-OC.sub.2 H.sub.5                                                                              C.sub.2 H.sub.5                                       419   3-OC.sub.2 H.sub.5                                                                              C.sub.2 H.sub.5                                       420   4-OC.sub.2 H.sub.5                                                                              C.sub.2 H.sub.5                                       421   2-OCH.sub.2 C.sub.6 H.sub.5                                                                     C.sub.2 H.sub.5                                       422   3-OCH.sub.2 C.sub.6 H.sub.5                                                                     C.sub.2 H.sub.5                                       423   4-OCH.sub.2 C.sub.6 H.sub.5                                                                     C.sub.2 H.sub.5                                       424   2-O-t-C.sub.4 H.sub.9                                                                           C.sub.2 H.sub.5                                       425   3-O-t-C.sub.4 H.sub.9                                                                           C.sub.2 H.sub.5                                       426   4-O-t-C.sub.4 H.sub.9                                                                           C.sub.2 H.sub.5                                       427   2-OC.sub.6 H.sub.5                                                                              C.sub.2 H.sub.5                                       428   3-OC.sub.6 H.sub.5                                                                              C.sub.2 H.sub.5                                       429   4-OC.sub.6 H.sub.5                                                                              C.sub.2 H.sub.5                                       430   2-CF.sub.3        C.sub.2 H.sub.5                                       431   3-CF.sub.3        C.sub.2 H.sub.5                                       432   4-CF.sub.3        C.sub.2 H.sub.5                                       433   2-OCF.sub.3       C.sub.2 H.sub.5                                       434   3-OCF.sub.3       C.sub.2 H.sub.5                                       435   4-OCF.sub.3       C.sub.2 H.sub.5                                       436   3-OCH.sub.2 CHF.sub.2                                                                           C.sub.2 H.sub.5                                       437   3-OCF.sub.2 CHF.sub.2                                                                           C.sub.2 H.sub.5                                       438   3-OC.sub.2 F.sub.5                                                                              C.sub.2 H.sub.5                                       439   2-NO.sub.2        C.sub.2 H.sub.5                                       440   3-NO.sub.2        C.sub.2 H.sub.5                                       441   4-NO.sub.2        C.sub.2 H.sub.5                                       442   2-CN              C.sub.2 H.sub.5                                       443   3-CN              C.sub.2 H.sub.5                                       444   4-CN              C.sub.2 H.sub.5                                       445   2-CH.sub.3, 3-Cl  C.sub.2 H.sub.5                                       446   2-CH.sub.3, 4-Cl  C.sub.2 H.sub.5                                       447   2-CH.sub.3, 5-Cl  C.sub.2 H.sub.5                                       448   2-CH.sub.3, 6-Cl  C.sub.2 H.sub.5                                       449   2-CH.sub.3, 3-F   C.sub.2 H.sub.5                                       450   2-CH.sub.3, 4-F   C.sub.2 H.sub.5                                       451   2-CH.sub.3, 5-F   C.sub.2 H.sub.5                                       452   2-CH.sub.3, 6-F   C.sub.2 H.sub.5                                       453   2-CH.sub.3, 3-Br  C.sub.2 H.sub.5                                       454   2-CH.sub.3, 4-Br  C.sub.2 H.sub.5                                       455   2-CH.sub.3, 5-Br  C.sub.2 H.sub.5                                       456   2-CH.sub.3, 6-Br  C.sub.2 H.sub.5                                       457   2-Cl, 3-CH.sub.3  C.sub.2 H.sub.5                                       458   2-Cl, 4-CH.sub.3  C.sub.2 H.sub.5                                       459   2-Cl, 5-CH.sub.3  C.sub.2 H.sub.5                                       460   2-F, 3-CH.sub.3   C.sub.2 H.sub.5                                       461   2-F, 4-CH.sub.3   C.sub.2 H.sub.5                                       462   2-F, 5-CH.sub.3   C.sub.2 H.sub.5                                       463   2-Br, 3-CH.sub.3  C.sub.2 H.sub.5                                       464   2-Br, 4-CH.sub.3  C.sub.2 H.sub.5                                       465   2-Br, 5-CH.sub.3  C.sub.2 H.sub.5                                       466   3-CH.sub.3, 4-Cl  C.sub.2 H.sub.5                                       467   3-CH.sub.3, 5-Cl  C.sub.2 H.sub.5                                       468   3-CH.sub.3, 4-F   C.sub.2 H.sub.5                                       469   3-CH.sub.3, 5-F   C.sub.2 H.sub.5                                       470   3-CH.sub.3, 4-Br  C.sub.2 H.sub.5                                       471   3-CH.sub.3, 5-Br  C.sub.2 H.sub.5                                       472   3-F, 4-CH.sub.3   C.sub.2 H.sub.5                                       473   3-Cl, 4-CH.sub.3  C.sub.2 H.sub.5                                       474   3-Br, 4-CH.sub.3  C.sub.2 H.sub.5                                       475   2-Cl, 4,5-(CH.sub.3).sub.2                                                                      C.sub.2 H.sub.5                                       476   2-Br, 4,5-(CH.sub.3).sub.2                                                                      C.sub.2 H.sub.5                                       477   2-Cl, 3,5-(CH.sub.3).sub.2                                                                      C.sub.2 H.sub.5                                       478   2-Br, 3,5-(CH.sub.3).sub.2                                                                      C.sub.2 H.sub.5                                       479   2,6-Cl.sub.2, 4-CH.sub.3                                                                        C.sub.2 H.sub.5                                       480   2,6-F.sub.2, 4-CH.sub.3                                                                         C.sub.2 H.sub.5                                       481   2,6-Br.sub.2, 4-CH.sub.3                                                                        C.sub.2 H.sub.5                                       482   2,4-Cl.sub.2, 6-CH.sub.3                                                                        C.sub.2 H.sub.5                                       483   2,4-F.sub.2, 6-CH.sub.3                                                                         C.sub.2 H.sub.5                                       484   2,4-Br.sub.2, 6-CH.sub.3                                                                        C.sub.2 H.sub.5                                       485   2,6-(CH.sub.3).sub.2, 4-F                                                                       C.sub.2 H.sub.5                                       486   2,6-(CH.sub.3).sub.2, 4-Cl                                                                      C.sub.2 H.sub.5                                       487   2,6-(CH.sub.3).sub.2, 4-Br                                                                      C.sub.2 H.sub.5                                       488   3,5-(CH.sub.3).sub.2, 4-F                                                                       C.sub.2 H.sub.5                                       489   3,5-(CH.sub.3).sub.2, 4-Cl                                                                      C.sub.2 H.sub.5                                       490   3,5-(CH.sub.3).sub.2, 4-Br                                                                      C.sub.2 H.sub.5                                       491   2,3,6-(CH.sub.3).sub.3, 4-F                                                                     C.sub.2 H.sub. 5                                      492   2,3,6-(CH.sub.3).sub.3, 4-Cl                                                                    C.sub.2 H.sub.5                                       493   2,3,6-(CH.sub.3).sub.3, 4-Br                                                                    C.sub.2 H.sub.5                                       494   2,4-(CH.sub.3).sub.2, 6-F                                                                       C.sub.2 H.sub.5                                       495   2,4-(CH.sub.3).sub.2, 6-Cl                                                                      C.sub.2 H.sub.5                                       496   2,4-(CH.sub.3).sub.2, 6-Br                                                                      C.sub.2 H.sub.5                                       497   2-i-C.sub.3 H.sub.7, 4-Cl, 5-CH.sub.3                                                           C.sub.2 H.sub.5                                       498   2-CH.sub.3, 4-Cl, 5-i-C.sub.3 H.sub.7                                                           C.sub.2 H.sub.5                                       499   2-Cl, 3-i-C.sub.3 H.sub.7                                                                       C.sub.2 H.sub.5                                       500   2-Cl, 4-i-C.sub.3 H.sub.7                                                                       C.sub.2 H.sub.5                                       501   2-Cl, 4-NO.sub.2  C.sub.2 H.sub.5                                       502   2-NO.sub.2, 4-Cl  C.sub.2 H.sub.5                                       478   2-Br, 3,5-(CH.sub.3).sub.2                                                                      C.sub.2 H.sub.5                                       479   2,6-Cl.sub.2, 4-CH.sub.3                                                                        C.sub.2 H.sub.5                                       480   2,6-F.sub.2, 4-CH.sub.3                                                                         C.sub.2 H.sub.5                                       481   2,6-Br.sub.2, 4-CH.sub.3                                                                        C.sub.2 H.sub.5                                       482   2,4-Cl.sub.2, 6-CH.sub.3                                                                        C.sub.2 H.sub.5                                       483   2,4-F.sub.2, 6-CH.sub.3                                                                         C.sub.2 H.sub.5                                       484   2,4-Br.sub.2, 6-CH.sub.3                                                                        C.sub.2 H.sub.5                                       485   2,6-(CH.sub.3).sub.2, 4-F                                                                       C.sub.2 H.sub.5                                       486   2,6-(CH.sub.3).sub.2, 4-Cl                                                                      C.sub.2 H.sub.5                                       487   2,6-(CH.sub.3).sub.2, 4-Br                                                                      C.sub.2 H.sub.5                                       488   3,5-(CH.sub.3).sub.2, 4-F                                                                       C.sub.2 H.sub.5                                       489   3,5-(CH.sub.3).sub.2, 4-Cl                                                                      C.sub.2 H.sub.5                                       490   3,5-(CH.sub.3).sub.2, 4-Br                                                                      C.sub.2 H.sub.5                                       491   2,3,6-(CH.sub.3).sub.3, 4-F                                                                     C.sub.2 H.sub.5                                       492   2,3,6-(CH.sub.3).sub.3, 4-Cl                                                                    C.sub.2 H.sub.5                                       493   2,3,6-(CH.sub.3).sub.3, 4-Br                                                                    C.sub.2 H.sub.5                                       494   2,4-(CH.sub.3).sub.2, 6-F                                                                       C.sub.2 H.sub.5                                       495   2,4-(CH.sub.3).sub.2, 6-Cl                                                                      C.sub.2 H.sub.5                                       496   2,4-(CH.sub.3).sub.2, 6-Br                                                                      C.sub.2 H.sub.5                                       497   2-i-C.sub.3 H.sub.7, 4-Cl, 5-CH.sub.3                                                           C.sub.2 H.sub.5                                       498   2-CH.sub.3, 4-Cl, 5-i-C.sub.3 H.sub.7                                                           C.sub.2 H.sub.5                                       499   2-Cl, 3-i-C.sub.3 H.sub.7                                                                       C.sub.2 H.sub.5                                       500   2-Cl, 4-i-C.sub.3 H.sub.7                                                                       C.sub.2 H.sub.5                                       501   2-Cl, 4-NO.sub.2  C.sub.2 H.sub.5                                       502   2-NO.sub.2, 4-Cl  C.sub.2 H.sub.5                                       503   2-OCH.sub.3, 5-NO.sub.2                                                                         C.sub.2 H.sub.5                                       504   2,4-Cl.sub.2, 5-NO.sub.2                                                                        C.sub.2 H.sub.5                                       505   2,4-Cl.sub.2, 6-NO.sub.2                                                                        C.sub.2 H.sub.5                                       506   2,6-Cl.sub.2, 4-NO.sub.2                                                                        C.sub.2 H.sub.5                                       507   2,6-Br.sub.2, 4-NO.sub.2                                                                        C.sub.2 H.sub.5                                       508   2,6-I.sub.2, 4-NO.sub.2                                                                         C.sub.2 H.sub.5                                       509   H                 H                                                     510   2-F               H                                                     511   3-F               H                                                     512   4-F               H                                                     513   2,3-F.sub.2       H                                                     514   2,4-F.sub.2       H                                                     515   2,4,6-F.sub.3     H                                                     516   2,3,4,5,6-F.sub.5 H                                                     517   2-Cl              H                                                     518   3-Cl              H                                                     519   4-Cl              H                                                     520   2,3-Cl.sub.2      H                                                     521   2,4-Cl.sub.2      H                                                     522   2,5-Cl.sub.2      H                                                     523   2,6-Cl.sub.2      H                                                     524   3,4-Cl.sub.2      H                                                     525   3,5-Cl.sub.2      H                                                     526   2,3,4-Cl.sub.3    H                                                     527   2,3,5-Cl.sub.3    H                                                     528   2,3,6-Cl.sub.3    H                                                     529   2,4,5-Cl.sub.3    H                                                     530   2,4,6-Cl.sub.3    H                                                     531   3,4,5-Cl.sub.3    H                                                     532   2,3,4,6-Cl.sub.4  H                                                     533   2,3,5,6-Cl.sub.4  H                                                     534   2,3,4,5,6-Cl.sub.5                                                                              H                                                     535   2-Br              H                                                     536   3-Br              H                                                     537   4-Br              H                                                     538   2,4-Br.sub.2      H                                                     539   2,5-Br.sub.2      H                                                     540   2,6-Br.sub.2      H                                                     541   2,4,6-Br.sub.3    H                                                     542   2,3,4,5,6-Br.sub.5                                                                              H                                                     543   2-I               H                                                     544   3-I               H                                                     545   4-I               H                                                     546   2,4-I.sub.2       H                                                     547   2-Cl, 3-F         H                                                     548   2-Cl, 4-F         H                                                     549   2-Cl, 5-F         H                                                     550   2-Cl, 6-F         H                                                     551   2-Cl, 3-Br        H                                                     552   2-Cl, 4-Br        H                                                     553   2-Cl, 5-Br        H                                                     554   2-Cl, 6-Br        H                                                     555   2-Br, 3-Cl        H                                                     556   2-Br, 4-Cl        H                                                     357   2-Br, 5-Cl        H                                                     558   2-Br, 3-F         H                                                     559   2-Br, 4-F         H                                                     560   2-Br, 5-F         H                                                     561   2-Br, 6-F         H                                                     562   2-F, 3-Cl         H                                                     563   2-F, 4-Cl         H                                                     564   2-F, 5-Cl         H                                                     565   3-Cl, 4-F         H                                                     566   3-Cl, 5-F         H                                                     567   3-Cl, 4-Br        H                                                     568   3-Cl, 5-Br        H                                                     569   3-F, 4-Cl         H                                                     570   3-F, 4-Br         H                                                     571   3-Br, 4-Cl        H                                                     572   3-Br, 4-F         H                                                     573   2,6-Cl.sub.2, 4-Br                                                                              H                                                     574   2-CH.sub.3        H                                                     575   3-CH.sub.3        H                                                     576   4-CH.sub.3        H                                                     577   2,3-(CH.sub.3).sub.2                                                                            H                                                     578   2,4-(CH.sub.3).sub.2                                                                            H                                                     579   2,5-(CH.sub.3).sub.2                                                                            H                                                     580   2,6-(CH.sub.3).sub.2                                                                            H                                                     581   3,4-(CH.sub.3).sub.2                                                                            H                                                     582   3,5-(CH.sub.3).sub.2                                                                            H                                                     583   2,3,4-(CH.sub.3).sub.3                                                                          H                                                     584   2,3,5-(CH.sub.3).sub.3                                                                          H                                                     585   2,3,6-(CH.sub.3).sub.3                                                                          H                                                     586   2,4,5-(CH.sub.3).sub.3                                                                          H                                                     587   2,4,6-(CH.sub.3).sub.3                                                                          H                                                     588   3,4,5-(CH.sub.3).sub.3                                                                          H                                                     589   2,3,4,6-(CH.sub.3).sub.4                                                                        H                                                     590   2,3,5,6-(CH.sub.3).sub.4                                                                        H                                                     591   2,3,4,5,6-(CH.sub.3).sub.5                                                                      H                                                     592   2-C.sub.2 H.sub.5 H                                                     593   3-C.sub.2 H.sub.5 H                                                     594   4-C.sub.2 H.sub.5 H                                                     595   2,4-(C.sub.2 H.sub.5).sub.2                                                                     H                                                     596   2,6-(C.sub.2 H.sub.5).sub.2                                                                     H                                                     597   3,5-(C.sub.2 H.sub.5).sub.2                                                                     H                                                     598   2,4,6-(C.sub.2 H.sub.5).sub.3                                                                   H                                                     599   2-n-C.sub.3 H.sub.7                                                                             H                                                     600   3-n-C.sub.3 H.sub.7                                                                             H                                                     601   4-n-C.sub.3 H.sub.7                                                                             H                                                     602   2-i-C.sub.3 H.sub.7                                                                             H                                                     603   3-i-C.sub.3 H.sub.7                                                                             H                                                     604   4-i-C.sub.3 H.sub.7                                                                             H                                                     605   2,4-(i-C.sub.3 H.sub.7).sub.2                                                                   H                                                     606   2,6-(i-C.sub.3 H.sub.7).sub.2                                                                   H                                                     607   2,4,6-(i-C.sub.3 H.sub.7).sub.3                                                                 H                                                     608   2,4,6-(i-C.sub.3 H.sub.7).sub.3                                                                 H                                                     609   2-s-C.sub.4 H.sub.9                                                                             H                                                     610   3-s-C.sub.4 H.sub.9                                                                             H                                                     611   4-s-C.sub.4 H.sub.9                                                                             H                                                     612   2-t-C.sub.4 H.sub.9                                                                             H                                                     613   3-t-C.sub.4 H.sub.9                                                                             H                                                     614   4-t-C.sub.4 H.sub.9                                                                             H                                                     615   2,3-(t-C.sub.4 H.sub.9).sub.2                                                                   H                                                     616   2,4-(t-C.sub.4 H.sub.9).sub.2                                                                   H                                                     617   2,5-(t-C.sub.4 H.sub.9).sub.2                                                                   H                                                     618   2,6-(t-C.sub.4 H.sub.9).sub.2                                                                   H                                                     619   3,5-(t-C.sub.4 H.sub.9).sub.2                                                                   H                                                     620   2,4,6-(t-C.sub.4 H.sub.9).sub.3                                                                 H                                                     621   4-n-C.sub.9 H.sub.19                                                                            H                                                     622   4-n-C.sub.12 H.sub.25                                                                           H                                                     623   3-n-C.sub.15 H.sub.31                                                                           H                                                     624   4-(1,1,3,3,-tetramethylbutyl)                                                                   H                                                     625   4-(1,1,3,-trimethylbutyl)                                                                       H                                                     626   2-t-C.sub.4 H.sub.9, 4-CH.sub.3                                                                 H                                                     627   2-t-C.sub.4 H.sub.9, 5-CH.sub.3                                                                 H                                                     628   2,6-(t-C.sub.4 H.sub.9).sub.2, 4-CH.sub.3                                                       H                                                     629   2-CH.sub.3, 4-t-C.sub.4 H.sub.9                                                                 H                                                     630   2-CH.sub.3, 6-t-C.sub.4 H.sub.9                                                                 H                                                     631   2-CH.sub.3, 4-i-C.sub.3 H.sub.7                                                                 H                                                     632   2-CH.sub.3, 5-i-C.sub.3 H.sub.7                                                                 H                                                     633   3-CH.sub.3, 4-i-C.sub.3 H.sub.7                                                                 H                                                     634   2-i-C.sub.3 H.sub.7, 5-CH.sub.3                                                                 H                                                     635   2,4-(t-C.sub.4 H.sub.9).sub.2, 6-i-C.sub.3 H.sub.7                                              H                                                     636   2-allyl (C.sub.3 H.sub.5)                                                                       H                                                     637   3-allyl           H                                                     638   4-allyl           H                                                     639   2-C.sub.3 H.sub.5, 6-CH.sub.3                                                                   H                                                     640   2-cyclo-C.sub.6 H.sub.11                                                                        H                                                     641   3-cyclo-C.sub.6 H.sub.11                                                                        H                                                     642   4-cyclo-C.sub.6 H.sub.11                                                                        H                                                     643   2,4-(cyclo-C.sub.6 H.sub.11).sub.2, 6-CH.sub.3                                                  H                                                     644   2-CH.sub.3, 4-cyclo-C.sub.6 H.sub.11                                                            H                                                     645   2-CH.sub.3,       H                                                           4-(1,1,3,3-tetramethylbutyl)                                            646   2-CH.sub.2 C.sub.6 H.sub.5                                                                      H                                                     647   3-CH.sub.2 C.sub.6 H.sub.5                                                                      H                                                     648   4-CH.sub.2 C.sub.6 H.sub.5                                                                      H                                                     649   2-CH.sub.2 C.sub.6 H.sub.5, 4-CH.sub.3                                                          H                                                     650   2-CH.sub.3, 4-CH.sub.2 C.sub.6 H.sub.5                                                          H                                                     651   2-C.sub.6 H.sub.5 H                                                     652   3-C.sub.6 H.sub.5 H                                                     653   4-C.sub.6 H.sub.5 H                                                     654   4-(2-i-C.sub.3 H.sub.7C.sub.6 H.sub.4)                                                          H                                                     655   4-C.sub.6 H.sub.5, 2,6-(CH.sub.3).sub.2                                                         H                                                     656   2-Cl, 4-C.sub.6 H.sub.5                                                                         H                                                     657   2-Br, 4-C.sub.6 H.sub.5                                                                         H                                                     658   2-C.sub.6 H.sub.5, 4-Cl                                                                         H                                                     659   2-C.sub.6 H.sub.5, 4-Br                                                                         H                                                     660   2-CH.sub.2 C.sub.6 H.sub.5, 4-Cl                                                                H                                                     661   2-CH.sub.2 C.sub.6 H.sub.5, 4-Br                                                                H                                                     662   2-Cl, 4-CH.sub.2 C.sub.6 H.sub.5                                                                H                                                     663   2-Br, 4-CH.sub.2 C.sub.6 H.sub.5                                                                H                                                     664   2-cyclo-C.sub.6 H.sub.11, 4-Cl                                                                  H                                                     665   2-cyclo-C.sub.6 H.sub.11, 4-Br                                                                  H                                                     666   2-Cl, 4-cyclo-C.sub.6 H.sub.11                                                                  H                                                     667   2-Br, 4-cyclo-C.sub.6 H.sub.11                                                                  H                                                     668   2-OCH.sub.3       H                                                     669   3-OCH.sub.3       H                                                     670   4-OCH.sub.3       H                                                     671   2,4-(OCH.sub.3).sub.2                                                                           H                                                     672   2-OC.sub.2 H.sub.5                                                                              H                                                     673   3-OC.sub.2 H.sub.5                                                                              H                                                     674   4-OC.sub.2 H.sub.5                                                                              H                                                     675   2-OCH.sub.2 C.sub.6 H.sub.5                                                                     H                                                     676   3-OCH.sub.2 C.sub.6 H.sub.5                                                                     H                                                     677   4-OCH.sub.2 C.sub.6 H.sub.5                                                                     H                                                     678   2-O-t-C.sub.4 H.sub.9                                                                           H                                                     679   3-O-t-C.sub.4 H.sub.9                                                                           H                                                     680   4-O-t-C.sub.4 H.sub.9                                                                           H                                                     681   2-OC.sub.6 H.sub.5                                                                              H                                                     682   3-OC.sub.6 H.sub.5                                                                              H                                                     683   4-OC.sub.6 H.sub.5                                                                              H                                                     684   2-CF.sub.3        H                                                     685   3-CF.sub.3        H                                                     686   4-CF.sub.3        H                                                     687   2-OCF.sub.3       H                                                     688   3-OCF.sub.3       H                                                     689   4-OCF.sub.3       H                                                     690   3-OCH.sub.2 CHF.sub.2                                                                           H                                                     691   3-OCF.sub.2 CHF.sub.2                                                                           H                                                     692   3-OC.sub.2 F.sub.5                                                                              H                                                     693   2-NO.sub.2        H                                                     694   3-NO.sub.2        H                                                     695   4-NO.sub.2        H                                                     696   2-CN              H                                                     697   3-CN              H                                                     698   4-CN              H                                                     699   2-CH.sub.3, 3-Cl  H                                                     700   2-CH.sub.3, 4-Cl  H                                                     701   2-CH.sub.3, 5-Cl  H                                                     702   2-CH.sub.3, 6-Cl  H                                                     703   2-CH.sub.3, 3-F   H                                                     704   2-CH.sub.3, 4-F   H                                                     705   2-CH.sub.3, 5-F   H                                                     706   2-CH.sub.3, 6-F   H                                                     707   2-CH.sub.3, 3-Br  H                                                     708   2-CH.sub.3, 4-Br  H                                                     709   2-CH.sub.3, 5-Br  H                                                     710   2-CH.sub.3, 6-Br  H                                                     711   2-Cl, 3-CH.sub.3  H                                                     712   2-Cl, 4-CH.sub.3  H                                                     713   2-Cl, 5-CH.sub.3  H                                                     714   2-F, 3-CH.sub.3   H                                                     715   2-F, 4-CH.sub.3   H                                                     716   2-F, 5-CH.sub.3   H                                                     717   2-Br, 3-CH.sub.3  H                                                     718   2-Br, 4-CH.sub.3  H                                                     719   2-Br, 5-CH.sub.3  H                                                     720   3-CH.sub.3, 4-Cl  H                                                     721   3-CH.sub.3, 5-Cl  H                                                     722   3-CH.sub.3, 4-F   H                                                     723   3-CH.sub.3, 5-F   H                                                     724   3-CH.sub.3, 4-Br  H                                                     725   3-CH.sub.3, 5-Br  H                                                     726   3-F, 4-CH.sub.3   H                                                     727   3-Cl, 4-CH.sub.3  H                                                     728   3-Br, 4-CH.sub.3  H                                                     729   2-Cl, 4,5-(CH.sub.3).sub.2                                                                      H                                                     730   2-Br, 4,5-(CH.sub.3).sub.2                                                                      H                                                     731   2-Cl, 3,5-(CH.sub.3).sub.2                                                                      H                                                     732   2-Br, 3,5-(CH.sub.3).sub.2                                                                      H                                                     733   2,6-Cl.sub.2, 4-CH.sub.3                                                                        H                                                     734   2,6-F.sub.2, 4-CH.sub.3                                                                         H                                                     735   2,6-Br.sub.2, 4-CH.sub.3                                                                        H                                                     736   2,4-Cl.sub.2, 6-CH.sub.3                                                                        H                                                     737   2,4-F.sub.2, 6-CH.sub.3                                                                         H                                                     738   2,4-Br.sub.2, 6-CH.sub.3                                                                        H                                                     739   2,6-(CH.sub.3).sub.2, 4-F                                                                       H                                                     740   2,6-(CH.sub.3).sub.2, 4-Cl                                                                      H                                                     741   2,6-(CH.sub.3).sub.2, 4-Br                                                                      H                                                     742   3,5-(CH.sub.3).sub.2, 4-F                                                                       H                                                     743   3,5-(CH.sub. 3).sub.2, 4-Cl                                                                     H                                                     744   3,5-(CH.sub.3).sub.2, 4-Br                                                                      H                                                     745   2,3,6-(CH.sub.3).sub.3, 4-F                                                                     H                                                     746   2,3,6-(CH.sub.3).sub.3, 4-Cl                                                                    H                                                     747   2,3,6-(CH.sub.3).sub.3, 4-Br                                                                    H                                                     748   2,4-(CH.sub.3).sub.2, 6-F                                                                       H                                                     749   2,4-(CH.sub.3).sub.2, 6-Cl                                                                      H                                                     750   2,4-(CH.sub.3).sub.2, 6-Br                                                                      H                                                     751   2-i-C.sub.3 H.sub.7, 4-Cl, 5-CH.sub.3                                                           H                                                     752   2-CH.sub.3, 4-Cl, 5-i-C.sub.3 H.sub.7                                                           H                                                     753   2-Cl, 3-i-C.sub.3 H.sub.7                                                                       H                                                     754   2-Cl, 4-i-C.sub.3 H.sub.7                                                                       H                                                     755   2-Cl, 4-NO.sub.2  H                                                     756   2-NO.sub.2, 4-Cl  H                                                     757   2-OCH.sub.3, 5-NO.sub.2                                                                         H                                                     758   2,4-Cl.sub.2, 5-NO.sub.2                                                                        H                                                     759   2,4-Cl.sub.2, 6-NO.sub.2                                                                        H                                                     760   2,6-Cl.sub.2, 4-NO.sub.2                                                                        H                                                     761   2,6-Br.sub.2, 4-NO.sub.2                                                                        H                                                     762   2,6-I.sub.2, 4-NO.sub.2                                                                         H                                                     763   2-CH.sub.3        n-C.sub.3 H.sub.7                                     764   2-CH.sub.3        i-C.sub.3 H.sub.7                                     765   2-CH.sub.3        cyclo-C.sub.3 H.sub.5                                 766   2-CH.sub.3        cyclo-C.sub.3 H.sub.5                                 767   2-CH.sub.3        cyclo-C.sub.5 H.sub.9                                 768   2-CH.sub.3        cyclo-C.sub.6 H.sub.11                                769   2-CH.sub.3        n-C.sub.4 H.sub.9                                     770   2-CH.sub. 3       i-C.sub.4 H.sub.9                                     771   2-CH.sub.3        s-C.sub.4 H.sub.9                                     772   2-CH.sub.3        t-C.sub.4 H.sub.9                                     773   2-CH.sub.3        n-C.sub.5 H.sub.11                                    774   2-CH.sub.3        n-C.sub.6 H.sub.13                                    775   H                 n-C.sub.3 H.sub.7                                     776   H                 i-C.sub.3 H.sub.7                                     777   H                 cyclo-C.sub.3 H.sub.5                                 778   H                 cyclo-C.sub.3 H.sub.5                                 779   H                 cyclo-C.sub.5 H.sub.9                                 780   H                 cyclo-C.sub.6 H.sub.11                                781   H                 n-C.sub.4 H.sub.9                                     782   H                 n-C.sub.5 H.sub.11                                    783   H                 n-C.sub.6 H.sub.13                                    784   *1)               CH.sub.3                                              785   *1)               C.sub.2 H.sub.5                                       786   *1)               H                                                     787   *2)               CH.sub.3                                              788   *2)               C.sub.2 H.sub.5                                       789   *2)               H                                                     ______________________________________                                         *1)                                                                           ##STR11##                                                                     *2)                                                                           ##STR12##                                                                

The aniline derivatives I are extremely effective on a broad spectrum ofphytopathogenic fungi, in particular those from the class consisting ofthe Ascomycetes and Basidiomycetes. Some of them have a systemic actionand can be used as foliar and soil fungicides.

The fungicidal compounds are of particular interest for controlling alarge number of fungi in various crops or their seeds, especially wheat,rye, barley, oats, rice, Indian corn, lawns, cotton, soybeans, coffee,sugar cane, fruit and ornamentals in horticulture and viticulture, andin vegetables such as cucumbers, beans and cucurbits.

The novel compounds are particularly useful for controlling thefollowing plant diseases:

Erysiphe graminis in cereals,

Erysiphe cichoracearum and Sphaerotheca fuliginea in cucurbits,

Podosphaera leucotricha in apples,

Uncinula necator in vines,

Puccinia species in cereals,

Rhizoctonia solani in cotton,

Ustilago species in cereals and sugar cane,

Venturia inaequalis (scab) in apples,

Helminthosporium species in cereals,

Septoria nodorum in wheat,

Botrytis cinerea (gray mold) in strawberries and grapes,

Cercospora arachidicola in groundnuts,

Pseudocercosporella herpotrichoides in wheat and barley,

Pyricularia oryzae in rice,

Phytophthora infestans in potatoes and tomatoes,

Fusarium and Verticillium species in various plants,

Plasmopara viticola in grapes,

Alternaria species in fruit and vegetables.

The compounds are applied by spraying or dusting the plants with theactive ingredients, or treating the seeds of the plants with the activeingredients. They may be applied before or after infection of the plantsor seeds by the fungi. It is possible to treat either the fungithemselves, or the plants, seeds, materials or the soil to be protectedagainst fungus attack.

The compounds can be converted into conventional formulations such assolutions, emulsions, suspensions, dusts, powders, pastes and granules.The application forms depend entirely on the purposes for which they areintended; they should at all events ensure a fine and uniformdistribution of the active ingredient. The formulations are produced inknown manner, for example by extending the active ingredient withsolvents and/or carriers, with or without the use of emulsifiers anddispersants; if water is used as solvent, it is also possible to employother organic solvents as auxiliary solvents. Suitable auxiliaries forthis purpose are solvents such as aromatics (e.g., xylene), chlorinatedaromatics (e.g., chlorobenzenes), paraffins (e.g., crude oil fractions),alcohols (e.g., methanol, butanol), ketones (e.g., cyclohexanone),amines (e.g., ethanolamine, dimethylformamide), and water; carriers suchas ground natural minerals (e.g., kaolins, aluminas, talc and chalk) andground synthetic minerals (e.g., highly disperse silica and silicates);emulsifiers such as nonionic and anionic emulsifiers (e.g.,polyoxyethylene fatty alcohol ethers, alkyl sulfonates and arylsulfonates); and dispersants such as lignin, sulfite waste liquors andmethylcellulose.

The fungicides generally contain from 0.1 to 95, and preferably from 0.5to 90, wt % of active ingredient. The application rates are from 0.02 to3 kg or more of active ingredient per hectare, depending on the type ofeffect desired. The compounds I may also be used for protectingmaterials (timber) e.g., against Paecilomyces variotii. When the activeingredients are used for treating seed, amounts of from 0.001 to 50, andpreferably from 0.01 to 10, g per kg of seed are generally sufficient.

The agents and the ready-to-use formulations prepared from them, such assolutions, emulsions, suspensions, powders, dusts, pastes and granules,are applied in conventional manner, for example by spraying, atomizing,dusting, scattering, dressing or watering.

Examples of formulations are given below.

I. A solution of 90 parts by weight of compound no. 1 and 10 parts byweight of N-methyl-α-pyrrolidone, which is suitable for application inthe form of very fine drops.

II. A mixture of 20 parts by weight of compound no. 1, 80 parts byweight of xylene, 10 parts by weight of the adduct of 8 to 10 moles ofethylene oxide and 1 mole of oleic acid-N-monoethanolamide, 5 parts byweight of the calcium salt of dodecylbenzenesulfonic acid, and 5 partsby weight of the adduct of 40 moles of ethylene oxide and 1 mole ofcastor oil. By finely dispersing the mixture in water, an aqueousdispersion is obtained.

III. An aqueous dispersion of 20 parts by weight of compound no. 4, 40parts by weight of cyclohexanone, 30 parts by weight of isobutanol, and20 parts by weight of the adduct of 40 moles of ethylene oxide and 1mole of castor oil. An aqueous dispersion is obtained by pouring thesolution into water and finely distributing it therein.

IV. An aqueous dispersion of 20 parts by weight of compound no. 68, 25parts by weight of cyclohexanol, 65 parts by weight of a mineral oilfraction having a boiling point between 210° and 280° C., and 10 partsby weight of the adduct of 40 moles of ethylene oxide and 1 mole ofcastor oil. An aqueous dispersion is obtained by pouring the solutioninto water and finely distributing it therein.

V. A hammer-milled mixture of 80 parts by weight of compound no. 4, 3parts by weight of the sodium salt of diisobutylnaphthalene-α-sulfonicacid, 10 parts by weight of the sodium salt of a lignin-sulfonic acidobtained from a sulfite waste liquor, and 7 parts by weight of powderedsilica gel. By finely dispersing the mixture in water, a spray liquor isobtained.

VI. An intimate mixture of 3 parts by weight of compound no. 68 and 97parts by weight of particulate kaolin. The dust contains 3 wt % of theactive ingredient.

VII. An intimate mixture of 30 parts by weight of compound no. 1, 92parts by weight of powdered silica gel and 8 parts by weight of paraffinoil sprayed onto the surface of this silica gel. This formulation of theactive ingredient exhibits good adherence.

VIII. A stable aqueous dispersion of 40 parts by weight of compound no.4, 10 parts of the sodium salt of a phenosulfonic acid-urea-formaldehydecondensate, 2 parts of silica gel and 48 parts of water, whichdispersion can be further diluted.

IX. A stable oily dispersion of 20 parts by weight of compound no. 1, 2parts by weight of the calcium salt of dodecylbenzenesulfonic acid, 8parts by weight of a fatty polyglycol ether, 2 parts by weight of thesodium salt of a phenosulfonic acid-urea-formaldehyde condensate and 68parts by weight of a paraffinic mineral oil.

In these application forms, the fungicidal agents according to theinvention may also be present together with other active ingredients,for example herbicides, insecticides, growth regulators, and fungicides,and may furthermore be mixed and applied together with fertilizers.Admixture with other fungicides often results in a greater fungicidalaction spectrum.

USE EXAMPLE EXAMPLE 1 5-Action on Pyrenophora teres

Barley seedlings of the "Igri" variety were sprayed to runoff at the2-leaf stage with aqueous suspensions containing (dry basis) 80% ofactive ingredient and 20% emulsifier. After 24 hours the plants wereinoculated with a spore suspension of the fungus Pyrenophora teres andplaced for 48 hours in a high-humidity climatic cabinet kept at 18° C.The plants were then cultivated for a further 5 days in the greenhouseat 20°-22° C. and a relative humidity of 70%. The extent of fungusspread was then determined.

The compound 2-phenoxymethylphenylglyoxylic acid methylester-O-methyloxime disclosed in DE-A-3,623,921 (compound no. 124) wasused for comparison purposes.

The results show that for instance compound no. 1 according to theinvention has a fungicidal action far superior to that of the prior artactive ingredient.

We claim:
 1. Aniline derivatives of the formula I ##STR13## where R ishydrogen, halogen, cyano, nitro, C₁ -C₁₅ -alkyl, C₃ -C₆ -cycloalkyl, C₃-C₆ -alkenyl, C₁ -C₄ -alkoxy, C₁ -C₂ -haloalkyl, C₁ -C₂ -haloalkoxy,substituted or unsubstituted phenyl, substituted or unsubstitutedphenoxy, benzyl, halobenzyl having up to three halo substituents, orsubstituted or unsubstituted benzyloxy, wherein the substituents ofsubstituted phenyl, substituted phenoxy, and substituted benzyloxy areup to 3 substituents independently selected from the group consisting ofhalo and C₁ -C₄ -alkyl,m is an integer of from 1 to 5 or the group##STR14## is α-naphthyl or β-naphthyl and X is hydrogen, C₁ -C₆ -alkylor C₃ -C₆ -cycloalkyl, or a plant-tolerated acid addition salt or metalcomplex thereof.
 2. An aniline derivative of the formula I as set forthin claim 1, where R_(m) is hydrogen and X is methyl.
 3. An anilinederivative of the formula I as set forth in claim 1, where R_(m) is4-fluorine and X is methyl.
 4. An aniline derivative of the formula I asset forth in claim 1, where R_(m) is 4-methyl and X is methyl.
 5. Afungicidal composition containing an inert carrier and a fungicidallyeffective amount of an aniline derivative of the formula I ##STR15##where R is hydrogen, halogen, cyano, nitro, C₁ -C₁₅ -alkyl, C₃ -C₆-cycloalkyl, C₃ -C₆ -alkenyl, C₁ -C₄ -alkoxy, C₁ -C₂ -haloalkyl, C₁ -C₂-haloalkoxy, substituted or unsubstituted phenyl, substituted orunsubstituted phenoxy, benzyl, halobenzyl having up to three halosubstituents, or substituted or unsubstituted benzyloxy, wherein thesubstituents of substituted phenyl, substituted phenoxy, and substitutedbenzyloxy are up to 3 substituents independently selected from the groupconsisting of halo and C₁ -C₄ -alkyl,m is an integer of from 1 to 5 orthe group ##STR16## is α-naphthyl or β-naphthyl and X is hydrogen, C₁-C₆ -alkyl or C₃ -C₆ -cycloalkyl, or a plant-tolerated acid additionsalt or metal complex thereof.
 6. A process for combating fungi, whereinthe fungi or the materials, plants, seed or the soil to be protectedagainst fungus attack are treated with a fungicidally effective amountof an aniline derivative of the formula I ##STR17## where R is hydrogen,halogen, cyano, nitron, C₁ -C₁₅ -alkyl, C₃ -C₆ -cycloalkyl, C₃ -C₆-alkenyl, C₁ -C₄ -alkoxy, C₁ -C₂ -haloalkyl, C₁ -C₂ -haloalkoxy,substituted or unsubstituted phenyl, substituted or unsubstitutedphenoxy, benzyl, halobenzyl having up to three halo substituents, orsubstituted or unsubstituted benzyloxy, wherein the substituents ofsubstituted phenyl, substituted phenoxy, and substituted benzyloxy areup to 3 substituents independently selected from the group consisting ofhalo and C₁ -C₄ -alkyl,m is an integer of from 1 to 5 or the group##STR18## is α-naphthyl or β-naphthyl and X is hydrogen, C₁ -C₆ -alkylor C₃ -C₆ -cycloalkyl, or a plant-tolerated acid addition salt or metalcomplex thereof.